Flighty Careers
Head of Operations & Finance
About Flighty
Flighty is the award-winning flight tracker trusted by frequent flyers, aviation nerds, and anxious travelers alike. We deliver real-time status, delay predictions, and beautiful visualizations that often beat the airline to the punch. Flighty is an Apple Design Award winner and App of the Year finalist, with a 4.8+ rating.
We are a tiny, elite, product-obsessed team distributed across the world. Our team spans 7 countries. We care deeply about details, honesty in our data, and shipping features that genuinely reduce stress for travelers.
We’re looking for a Head of Operations & Finance to own the business side of Flighty.
The company is profitable, growing, and intentionally small. The product has strong product–market fit and a loyal global user base. What we need now is someone to fully own how the business runs, so the founding team can stay focused on building the best flying experience in the world.
This is a COO-style role for a small, high-performing company. You will oversee finance, operations, marketing efficiency, partnerships, and people operations to ensure the company runs smoothly and intelligently as it grows.
You will start as a hands-on individual contributor across these areas. As needs arise, you will have the authority to hire and manage specialized support (e.g., accounting, HR, marketing) where it creates leverage.
You’ll sit at the leadership table from day one, with real responsibility for financial planning, operational systems, and the strategic decisions that shape how the company operates.
Because the team is intentionally small, this is a hands-on executive role. You won’t be managing large teams or sitting in meetings all day. You will be building models, negotiating partnerships, improving reporting, and making decisions that directly shape how the company operates.
You will have full visibility into the company’s performance and the authority to improve how it runs. The role is not about managing layers of people. It’s about owning the mechanics of a successful software business and ensuring it continues to operate efficiently and intelligently.
This role exists so that the business side of Flighty is run with the same care and rigor as the product itself.
This role is ideal for you if…
You long for hands-on, individual contributor role that happens to carry executive-level responsibility.
You're a generalist who goes deep. You can negotiate a B2B partnership, model a pricing change, and reconcile Q3 tax estimates. That’s just a Monday and you prefer it that way.
You understand the mechanics of App Store subscription businesses: revenue recognition, platform fees, refund rates, cohort analysis, LTV modeling.
You're comfortable with ambiguity and low structure. There is no playbook. There is no team to delegate to. There's a founder who needs more focus, and a business that needs an operator.
You have strong opinions about how things should work and the ability to implement them yourself. We don't have procurement. If you think we need a better dashboard, go build it.
What you'll do
You will own:
Compliment the Founder CEO’s core competencies, by owning Finance and Operations.
Own P&L, SaaS KPI’s, modeling, performance marketing metrics.
Own B2B and partnerships. Develop go-to-market strategies, including vertical/segment prioritization, expansion, solution packaging, and pricing.
Ensure data accuracy, accessibility, and analytics as the foundation for insights and optimization.
Performance marketing efficiency and spend strategy.
People operations (hiring, compensation, basic compliance).
You will directly execute (especially early):
Financial modeling and reporting.
Building and maintaining dashboards and KPI systems.
Vendor selection and management.
Performance marketing oversight (hands-on or close to it).
You will build over time:
External or internal support for accounting, HR, and marketing.
Scalable systems that reduce manual work.
Simple, effective processes across business functions.
What success looks like
In the first 90 days:
Take over monthly financial reporting package, including outsourced bookkeeping.
Take over business KPI platforms, tracking, and reporting. eg. new revenue, retention, CAC, LTV.
You've identified the top 3–5 operational gaps and have a plan to close them.
The CEO has stopped doing ops work and trusts you to handle it.
In the first 180 days:
Financial reporting and dashboards exist where they didn't before—leadership gets a monthly snapshot without asking.
Lead B2B go-to-market strategy and prioritization.
Manage performance marketing spend, spend strategies, channel.
What we're looking for
Must have:
Strong preference for Austin, TX resident otherwise working CST standard hours.
High bar in everything you do. Every detail matters. You say what you mean and do what you say. You listen intently, love collaborating with experts, and your work is part of your identity.
8+ years in operations, finance, strategy, or similar roles. Preferably bootstrapped.
Experience as the "business person" at a small, profitable software company—ideally a consumer subscription product. Owned P&L and company reporting package top to bottom. Not a consultant. Not a banker. Not a big-company finance director. Someone who has actually run the business side of a product company.
Deep financial literacy beyond basic bookkeeping. You understand revenue recognition, subscription economics, platform fees, LTV modeling, cohort analysis, and tax strategy at a C-Corp level. You're not learning this on the job.
Comfortable operating in small teams where you are responsible for multiple functions.
Clear thinking, high integrity, and strong ownership mentality.
Genuine interest in aviation experiences across the globe.
Nice to have:
Experience with iOS App Store / subscription products.
Performance marketing experience.
Experience working in distributed or international teams.
What this role is not:
Not a people management role with large teams.
Not a purely finance/accounting role.
Not a specialized marketing or growth role.
Final note:
This role is best suited for someone who enjoys building the infrastructure of a company—not just managing it once it exists.
What we offer
Top quartile salary with a meaningful performance bonus tied to company results.
Flexible and generous paid time off.
Health insurance (US).
World travel for quarterly exec retreat and annual team retreat.
The opportunity to directly shape a profitable, influential product.
How to apply
Please email [email protected] using the job title as your subject line. Please include your name, where you live, LinkedIn profile, a portfolio website (if relevant), your resume, and details on why you want to join Flighty.
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Come be part of an award-winning team
Apple Design Award
Winner 2023
App of the Year
Finalist 2023
